


Purgatory Blues

by Catatonic_SXE



Category: Supernatural
Genre: Anal Sex, Cas is one jealous son of a bitch, Cock Cage, Daddy Kink, Eventual Threesome, M/M, M/M/M, Oral Sex, Panty Kink, Punishment/Reward, Top!Benny, Top!Cas, awkward kitchen chit chat, bottom!Dean, clumsy handjob, dean is actually very okay with this punishment, grace fucking, he's gonna go full slut soon, i should have skipped season eight, im sorry but I love making Dean a slut, just wait, kinky fucker, prostate milking technically
Language: English
Status: In-Progress
Published: 2016-06-12
Updated: 2016-06-17
Packaged: 2018-07-14 16:14:03
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 4,934
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7179485
Author URL: https://archiveofourown.org/users/Catatonic_SXE/pseuds/Catatonic_SXE
Summary: <blockquote class="userstuff">
              <p>Dean and Benny really did have something in purgatory, but it wasn't exactly pure. After they got out, they start back up again. It wasn't exactly romance, but neither of them are complaining. The only one complaining is a jealous angel that missed his chance. Or did he?</p><p>In which I've just started season eight and I've got a huge kink for Cas being jealous as fuck of Benny.</p><p>Note: Since it's split on how everyone wants this to end, and I'm a little torn myself, this story will have two endings.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I should have skipped this season I'm a sinning mess rn. I'll add more tags as the sin continues.

Dean curled his fingers into the thin, off white motel bed sheets and let out a long, rather high pitched whine as thick, callused fingers worked his hole open, curling a little inside him and just barely missing his prostate. Knowing Benny, it was on purpose. 

"Listen to you, sugar. You sound so pretty."Benny said into the crook of Dean's neck, keeping Dean's chest pressed down into the mattress. The full weight of him on his back, the way Benny could maneuver him into just about any position, it made Dean feel a little along the lines of a rag doll. 

And he was completely okay with this. 

"Daddy please..."he tried to arch back into him, but Benny was still pressing down hard."Daddy please, what? Tell daddy what you need."Benny crooked his fingers again, purposely missing again."You need daddy's cock? Need for daddy to split you open, fuck you til you cry?"

Dean shuddered, his cock was leaking through the panties Benny had him put on earlier that day. Pink and lacy, somewhere in the back of his mind Dean had been debating wearing them all the time, they felt that good. 

He nodded, barely managing to get out a 'please' before Benny pulled his fingers out, leaving Dean open and empty and needy. 

Benny moved him, spreading his legs a little more, taking a second to admire how he trembled with anticipation."So damn pretty..."he said, more to himself as one hand ran up the back of Dean's thighs, lightly dragging his nails up the smooth, bare skin. The other hand was busy slicking up his cock, he didn't want to hurt Dean any more than the young hunter wanted him to. 

Dean was still trying to arch back into him, rather enjoying how easily Benny had him pinned under his weight. His hand moved from Dean's thighs to his shoulder, holding him in place.

Benny couldn't help how slow he pushed inside him, reveling in how Dean gasped and how he fisted his hands in the sheets again. Benny was thick, much thicker than his fingers and it burned, the way he was already stretching him out. 

"F-fuck...daddy..."he arched, finally able to push back against him, trying to take more of him."Ah ah...slow down sugar, or you ain't gonna be doin much walkin tomorrow."Benny put a firm hand on his hip, keeping Dean from pushing and taking any more. He wouldn't keep it this slow, but if he started in fucking him like that, Dean wouldn't be doing anything for the next couple days. That had been the plan until he felt Dean clench around his cock, the heat of it making Benny dizzy for a moment. 

He didn't wait to let Dean to fully adjust before he started in on shallow thrusts, holding tight onto his hip and using it to pull Dean back on him like he wanted. He dropped his head into the sheets and let out a series of unintelligible half word, half moans.

Benny hooked an arm under him, pulling him up and putting Dean flat on his stomach as his pace started in a little rougher, yanking his panties a little more off his ass. Dean couldn't do much of anything aside from the string of begging that came from him when Benny really started to fuck him. The sound of flesh slapping against flesh was absolutely obscene every time it hit Dean's ears, it mixed all too perfectly with little grunting noises Benny was making above him. 

"Daddy!"he couldn't help screaming out when he angled differently, aiming for his prostate with every snap of his hips. This new angle pushed him further into the mattress, his cock rubbing against his panties every time he moved. 

"There it is..."Benny murmured between grunts, hips moving at an unforgiving pace, snapping forward at an almost inhuman speed. 

That's all Dean could manage to yammer out, over and over. He felt heat slowly spread and tighten in his belly as he felt his orgasm slowly start to build.

"W-wanna...daddy, please!"he couldn't help how his hips rutted against the mattress, pathetically trying for enough firction to come. Benny smirked, changing the pace to further drive Dean's hips against the mattress."Go on, sugar..."he said roughly against Dean's ear, the scruff of his beard rubbing against him,"Make a mess in those pretty panties."

As soon as the words left Benny's mouth, Dean's body went rigid as his orgasm tore through him, shuddering as he felt his panties become warm and wet against his skin. Benny fucked him throughly through his orgasm before he pulled out, causing the hunter to whine at the lose. 

Before Dean could catch his breath and ask what he was doing, Benny had him on his back so he was looking up at him. The boy was flushed red, sweaty, and fucked out.

"Open your mouth."Benny said, moving up closer, hand lazily stroking his cock. Dean knew exactly where he was going and let his lips part, tongue out and waiting. Benny let out a couple soft moans as he stroked himself to completion, painting Dean's lips, cheeks, and chin white as he came. 

"Look at you..."he panted softly as Dean tried to lick up as much of it as he could before he started using his fingers."Does daddy taste good?"Dean's face flushed a deeper red and he nodded. 

A little over an hour later, Dean was freshly showered and redressed, Benny about halfway so. He shifted a moment, suddenly unsure of how to say goodbye in situations like this. Benny was one step ahead of him, holding the back of his neck tightly as he kissed him. He could still faintly taste himself on Dean's tongue. 

"You know how to find me..."

Dean nodded, saying a quiet goodbye before he left. 

Benny was alone now, but not completely. 

"You think I didn't know you were watching?"he said into the empty air. The presence he was addressing made themselves very visible. 

Castiel. And he was angry, his fists clenched, face twisted into a dark scowl. His eyes may have been a deeper blue, but they had never seemed so icy."You have no idea how much I would love to send you back into purgatory."he said. 

"You wouldn't. You don't want to piss him off."Benny said with a smug little smirk, leaning back against the wall."You're just hot because I got to him before you did. You've been dying for that for so long, and here I am, barely knowing him and he'll bend over for me in a heartbeat."

Cas couldn't tell him he was wrong. While it was a fairly new feeling, he knew it was jealousy that had him."You can't have him."

"I'd discuss that with Dean, see what he has to say about it."Benny said, pulling the rest of his clothes together. He turned as he put his coat on, but the angel was already gone. 

He wasn't about to give Dean up without a fight.


	2. Chapter 2

**Summary for the Chapter:**

> In which Cas learned from both the Pizza Man and the Babysitter and Dean finds a loophole.

Dean pulled a beer out of the fridge, glad Sam out collecting information a couple towns away. He needed a little time to himself, especially since he couldn't get Benny off his mind. He had never had sex that intense before and his body was still a little wobbly a couple days after the fact. 

Every time he closed his eyes, he could still feel Benny inside him. He shuddered, thinking of how rough he'd been as he walked back to his bedroom, setting his beer down before flopping down on his bed.

Dean's eyes fluttered a moment but remained closed and he slipped the tips of his fingers under the waist of his jeans. Under the denim was lace, the same panties he had worn with Benny. Dean felt his cock twitch and he cursed under his breath. He'd given Dean one rule for when they were away and only one. No touching. He groaned and dropped his head back against his pillow. If he had known it was going to be this hard, no pun intended, he wouldn't have let Benny set any kind of rules. 

Of course, he could get himself off, no problem. But Benny somehow always knew when he lied about it, snd then over his knee Dean went. Not that he didn't enjoy it sometimes, but he preferred to not start their nights together like that. 

His cock throbbed against the lace and the denim and Dean dug his palms into his eyes. He needed to stop thinking about it or there would be no fixing the situation. Maybe if he called and asked for permission, beg a little, Benny would let it slide just this once. Or he'd tell him no and punish him anyways next time. 

Dean decided, since he was indeed alone, to just at least release the pressure. He popped the button open on his pants and slid the zipper down so he could wiggle out of his jeans a little bit. The throbbing didn't stop, but thankfully his cock wasn't pushing flush against the denim anymore. He let out a soft whine at the slight relief and leaned back against his bed again.

Dean's eyes flew open on instinct and he grabbed a pillow to cover his crotch, a mistake he realized when the pillow rubbed against him. He stifled a whine as he sat up. 

"Dammit Cas you can't come in here like that!" Dean's face was flushed a bright scarlet, he didn't know how to offer an explanation for what Cas could have seen. 

Lie. Cas told himself. 

"I...felt you in distress, Dean. I didn't know you...you were uh..."he glanced down at the pillow between Dean's legs.

"I wasn't."he shot back quickly. 

"Well I would...recommend it."

Dean didn't want to have this conversation, least of all with Cas, but his head was far too cloudy to form any sort of rebuttal to what he said. Cas kept looking down at the pillow between his legs, lips parted a little and inside Dean's hazy imagination, he briefly wondered how those pretty pink lips would feel around his cock. 

Cas's eyes lifted from the pillow to meet Dean's gaze."I...could help."he offered, completely throwing Dean off. He shook his head weakly."I can't."why was this still in discussion, Dean couldn't keep himself from talking."He told you that you couldn't...didn't he?"Dean's eyes widened in surprise."How did you-"

"I can feel his presence on you."another lie, but Dean was too out of it to tell the difference between the truth and a blatant lie.

Fuck. He knew. But Dean's body was reacting in an entirely different manner. Benny was going to rip him a new one, figuratively and literally, but there was a loophole. He wasn't getting himself off, so that had to count for something. 

Dean nodded, letting out a little 'please', looking up at Cas with his bottom lip between his teeth. Watching the angel walk over to the edge of his bed felt like it took a thousand years as the anticipation set in. 

Cas pulled his trench coat and suit jacket off at the same time, not caring much where they fell. Dean broke his gaze for a moment to watch him toss them down before he felt a strong grip pull him to the edge of the bed, letting out a little gasp as he felt his body lurch forward. He hadn't been expecting Cas to pull him like that. Dean looked back up to see Cas sinking to his knees as he loosened the tie around his neck, a few buttons followed to give his neck room to move. 

The pillow was gone, he felt Cas's hands pulling his jeans further down. His face turned a bright red in realization at what else he was wearing. But the angel's fingers curled around the lace, muttering a soft 'so pretty' as he pulled Dean's panties off his hips, tugging them down far enough to free his cock.

Cas looked up at him, those deep blue eyes sparkling as if he was asking permission, though he already had it. 

"Cas please..."

That was all he needed to hear. He licked his lips before turning his attention to Dean's cock, slowly rolling his tongue over the head. The shudder from above told him keep going. He repeated this action a few more times before wrapping his lips around the head to suck lightly, earning what sounded like a mix of a moan and a whine. Whatever that noise was, Cas felt his own cock twitch at Dean's reactions.

His mouth was hot, it contradicted Benny's cooler mouth drastically. Deans hand immedietely found a loose grip on Cas's hair, wanting so badly to pull him down further on his cock. He was certain Cas wasn't that used to something like this, best not to push him. 

Cas gently wrapped his hand around the base, using his grip to slowly work more of Dean into his mouth and down his throat. He hollowed his cheeks, letting out a low moan when he felt Dean twitch near the back of his throat. A high pitched whine came from deep within Dean's chest, tearing out of him before he could stop himself. 

He took as much of Dean back as he could before he started to slowly bob his head, working what he couldn't fit in his mouth with his hand. His hand tightened in Cas's hair, resisting the urge to buck himself down his throat. His lips parted and he moaned out his name, unable to say much else. Full name, nickname, it spilled from Dean's mouth like a filthy prayer as the angel continued to suck and stroke him. 

Dean felt that familiar tightening in his stomach and let out a pathetic whine, failing as he started bucking shallowly down Cas's throat."S-stop...I'm..."Dean yammered, unknowing at how willing Cas was to let him finish down his throat.

Cas didn't pull away, instead he relaxed his throat as best he could, allowing Dean to fuck his throat as he neared his orgasm. 

Soon enough, it was over. Dean came, hard, spilling down Cas's throat, who worked to make himself swallow as much of it as he could. His hips twitched pathetically as he gasped out his name, head rolling back a little. 

Cas let him finish before he slowly pulled away from him, wiping the cum and spit from his mouth with the sleeve of his shirt. Dean's eyes were closed, head tipped back as he worked to catch his breath.

"Cas..."he murmured softly, picking up his head to look down at him on the floor. 

The Angel was gone, clothes and all. Dean went quiet, the only sound in the room was his soft panting and the sound of him redressing himself. The haze in his mind has cleared, unsure of what exactly had just happened. He laid back on his bed, arm over his eyes, unable to keep the slideshow of Benny and Cas out of his mind, effectively putting him back in the same boat as when he started. 

This time, he'd have to take care of it himself and face the consequences with Benny later.


	3. Chapter 3

**Summary for the Chapter:**

> Dean reflects on his punishment.
> 
> ('Flashback')

It wasn't any shock to Dean that Benny could tell he was lying when he said he hadn't gotten off while they were apart. He left out the part about Cas, because throwing the Angel under the bus wasn't going to make the situation any better, not by a long shot. 

That's how Dean ended up back in the bunker after meeting up with Benny. It had been torturously brief.

'Benny closed the motel door behind Dean as he entered, shaking his head. He looked...disappointed. And Dean knew he could sense it on him still, even though it had been yesterday. He could still pick that post orgasmic glow off of Dean. No matter how faint it must have been now. 

One of the perks to being a monster, he guessed. 

"You're always such a good boy for daddy...you haven't been very good this time, have you?"the thick drawl of that Louisiana accent hit him right in his core, causing him to shiver. 

Dean felt himself drop immedietely into submission, head down as he shook his head."I...it hurt so bad...I had to."he confessed weakly. It hadn't been a lie. Dean's whole body had been aching, even if Cas hadn't have come in like that, he would have taken care of it himself. 

Benny clicked his tongue in disapproval, slowly walking toward the hunter. Dean didn't look up, he knew he had disappointed him and he knew that this side of him would do anything to please Benny to make up for it. 

"I don't think a spanking is going to do the trick this time, sugar."Dean let out a soft whimper, glancing up at the vampire as he walked toward him."Maybe something a little more...prolonged, should do the trick."

Whatever was about to happen, Dean told himself in the back of his mind,'You were bad. You deserve it. He's not going to hurt you. It's just a punishment.'

"Lay down for daddy, sugar. On your back."Benny instructed. Dean did as he was told, backing up into the mattress and falling back, keeping his eyes on Benny. 

The vampire's gaze was fixed on the front of Dean's pants. He clicked his tongue again."Take them off."Dean didn't hesitate in pulling his jeans down and off, blushing as he realized in his haste to meet with Benny, he's forgotten Benny's favorite part of it all. 

"No panties...were you really that eager, knowing you were gonna be punished?"Benny's words drawled out as he fiddled with something in his pocket. Dean shook his head,"I didn't want to be late..."Dean knew it would have been worse if he was late, he had jumped out of the shower, thrown clothes on, and bolted. His hair was still wet, even. 

Benny took note of his appearance and nodded."I'll forgive you for that, but just this once."he said, stopping a few feet short of the bed, eyes on Dean's cock.

"This won't do...daddy needs you soft for this. Think you can fix that for me?"

Dean bit his lip and nodded."Y-yes daddy..."

Dean closed his eyes and slowly wrapped his hand around his cock, stroking slowly. Somewhere in the back of his mind, images between Benny and Cas flickered back and forth like a strange, erotic double feature. It went back and forth between the way Benny fucked him raw, hard and the gentle caresses Cas's hands, the way his mouth felt around his cock. It flickered back and forth so much, sped through so quickly, that it became one image. Riding Benny, letting the vampire slam him down hard while Cas worked his cock. 

Dean came fast, more from the mental image than from the rhythm of his own hand. 

He looked down at the mess on his hand, on his shirt, then looked back up at Benny, lip still between his teeth. His teeth had dug so hard into his lip that little droplets of blood formed against the rosy flesh of his lips. 

Benny let out a little groan, cocking his head to the side as pushed Dean back down against the bed so hard that he bounced against the cheap mattress. 

"Now daddy's gonna put this on you...it's for your own good, understand?"he said, pulling a little silver cage out of his pocket. Dean let out what was supposed to be a moan, but it came out more as a stuttered whine. He nodded, relaxing. 

Benny put the cage on Dean with little difficulty, the Hunter mewling underneath him at the feeling of the cool metal against the sensitive flesh of his cock. 

"Good boy, sitting still for me..."Benny cooed once he had it on him."Now why don't you be really good and help daddy take care of a little problem."Dean nodded, letting Benny sit on the motel bed as he sank to his knees.' 

Dean snapped out of it, hand pressing lightly against his crotch, making sure the cage wasn't visible through his jeans. He shifted, eyes fluttering a little as his jeans rubbed him through it. 

"One week..."he muttered under his breath. 

"One week til what?"Sam asked as he walked into the room, tossing a folder down as he took his seat."Dr. Sexy coming back?"he laughed. 

"I uh...yeah."Dean said, scooting his chair in to further hide himself from Sam.

"Cas said he's on his way in, he has information on the case."Sam said as he flipped through the file spread out in front of him. Dean felt his body stiffen, he hadn't seen or heard from Cas since a few nights ago. The last time he had seen him was when he was on his knees, Dean's cock in his mouth. 

These next few hours would be absolute tortute after what he'd been through earlier.


	4. Chapter 4

**Summary for the Chapter:**

> Even Dean somehow can manage to find a way around punishment.

**Notes for the Chapter:**

> This took forever and I am so sorry. Too much going on. So I took a minute to hammer this out while eating chocolate cake from the gas station. :')

Dean had to have the worst luck with the way the last few days had gone. The incident with Cas, Benny's reaction to the half truth of it, and now Sam decided to take the absolute worst time to take off on a food run.

He could feel Cas's blue eyes practically burning into him. Dean hadn't opened his mouth since he left, he couldn't bring himself to look over at Cas, mostly out of his own embarrassment at how the angel had caught him. He was comfortable with the awkward silence. 

"So I take it...Sam is doing well with the trials?"Cas finally spoke up, the sound of his voice causing Dean to jump a little."He's not. But once this is all over, everything will be just fine."he said, hoping his answer would suffice and they could lapse back into silence.

Dean was very wrong about that. 

"I...Dean, we need to talk."

His face turned a bright shade of pink, knowing exactly what the Angel was referring to. He simply shook his head."We don't need to talk about anything, Cas. It was a one time thing. And even then, it was an accident."he said this all in one breath, sucking in to fill his lungs back up. He still couldn't look at him from across the table. 

"Is he good to you?"

This question caught the hunter fully off guard and he finally raised his head to look up. 

"What do you mean, 'is he good to me'?"Dean asked."I know he...satisfies you. But does he take care of you?"Cas didn't realize it, but the amount of concern on his face was unsettling.

"I mean...it's not..."Dean didn't know quite how to explain it."It's not...actually a relationship, I guess. So there's not much to take care of."he said eventually, hoping again that this would satisfy him and they could get back to work. 

It was silent for a few moments only before Cas started in again,"The way he does...take care of you, you enjoy it?"

Dean wanted nothing more than to drop his head on the desk and disappear. He didn't want to sit and talk out his kinks with an angel, but there was always something about Cas that compelled him to answer."I...yeah, I do."he sighed, rubbing the back of his neck awkwardly. The roughness, the punishment, the praise, the toys, all of these things found he very much did enjoy with Benny. Though he was a vampire, he was still a man. One that had no qualms with putting Dean in his place. 

He pulled himself away from his thoughts rather quickly, not wanting to see how much pressure he could take from the cage.

Cas watched Dean close his eyes and take his bottom lip between his teeth. His face was flushed a soft pink, and the look of halfway concentration was as if he was trying to fight something off, like the night Cas 'took care of him'.

"I could...help again, if you are in discomfort."he offered, unable to place a real word to Dean's situation. Dean snapped out of his daze, registering reality enough to shake his head."I...you can't."Dean pressed gently against the cage, shivering when he pressed too hard. 

"I can if you allow me."

Dean was sure Cas didn't mean for it to sound that suggestive, but it made his cock twitch inside the cage, almost painfully. And he liked it. 

"Cas..."

The angel had to keep himself in check with the way Dean said his name. The neediness of it."Shall we...go to your room?"Cas asked. Dean was already out of his seat and halfway there. 

/////

The noises that filled the room were almost all Dean's. Little whimpers and sighs, most of them Cas trying to swallow as he kissed him. Dean was clawing at his shoulders and his chest, needy in his physical contact. 

Cas couldn't help it, he grabbed Dean by the wrists and pinned them above his head."Don't move."he instructed gently. Dean nodded, stating up at Cas with glassy eyes. He managed to pull Dean's pants away, a little disappointed when he saw that Dean wasn't wearing panties like he had been before. 

Cas's eyes fell on the cage. He knew Dean wouldn't want him to take it off, but there was still a way around it, for Dean to still be pleased. Cas loosened his grip on Dean's wrists but he didn't let them go. His knee moved to spread Dean's legs a little, avoiding bumping the cage. 

"Look at me..."Cas again gave him instruction in a soft tone, something Dean wasn't particularly used to. He gazed up at th angel, wondering what would come next. 

That question was answered rather quickly as Dean felt his hole stretch around what he knew was nothing. He cried out, trying to keep his eyes on Cas as his body arched involuntarily. Had he been in his right mind, he would have known it was Cas's grace that he was stretched around, that was filling him and rubbing hard already against his prostate. 

"A-ah...fuck...Cas!"Dean whined out, rolling his hips into it. If Cas pushed any harder, this wasn't going to last long at all. 

The angel couldn't take his eyes off of him, loving every little twitch and moan that came from below. He could feel Dean inside, through his grace, and the heat of him inside made Cas almost dizzy. Dean's eyes were glassy as he started to buck his hips, riding at nothing and everything all at once. The cage around his cock grew tighter around him but it barely registered with him. 

"More...Cas please, more."the whine in his voice could have had Cas come undone right there. But this was about Dean and making sure he got the pleasure he deserved. He manipulated his grace to driv harder into him, causing tears to well up in Dean's eyes from the sheer blinding pleasure of what Cas was doing to him. 

His cock was leaking through the cage, dripping all on his stomach and he tried to ride it faster, causing the cage to bounce a little, again, barely registering as Dean felt an orgasm building up inside him. 

"I...please. I-I wanna..."he couldn't quite get the words out, but Cas still knew what he wanted."You're okay...go on."he murmured in Dean's ear. 

Dean came, through the cage as Cas continued to slowly fuck him like this. He moaned out his name over and over. Cas would never get over how he loved to hear Dean say his name. His orgasm took almost everything out of him, surprised through his daze that he was even able to cum like that with this on his cock. 

Cas let him ride it out before his grace faded and he went to slowly move off of Dean. He felt a hand wrap around his wrist and a small tug pull him down back on top of him."Not yet..."Dean wouldn't let him go, not without returning the favor. 

With Cas still on top of him, Dean's fingers fumbled to undo the belt around his waist and unzip the slacks to tug them and Cas's underwear down just enough for Dean to wrap his hand around the Angel's cock. 

"Dean..."the moan was deep, his fingers dug into the sheets as he worked to keep himself upright. The hunter's hand was clumsy in his post orgasmic state but he still worked hard, stroking Cas to completion. It didn't take very long before he came on Dean's stomach, mixing with the boy's mess from moments ago. 

The two of them laid like that for a moment, working to right their breathing and return to a somewhat normal state to assess the 'situation'.

While Cas was working to put the both of them back together, Dean's mind was hazily scheming, searching for a way to ask Benny to fulfill a new dirty little fantasy he had brewing in his head. 

This next week would get very interesting.


End file.
